Santa Ana winds (SAWs) are associated with anomalous temperatures in coastal Southern California (SoCal). As dry air flows over SoCal’s coastal ranges on its way from the elevated Great Basin down to sea level, all SAWs warm adiabatically. Many but not all SAWs produce coastal heat events. The strongest regionally averaged SAWs tend to be cold. In fact, some of the hottest and coldest observed temperatures in coastal SoCal are linked to SAWs. We show that hot and cold SAWs are produced by distinct synoptic dynamics. High-amplitude anticyclonic flow around a blocking high pressure aloft anchored at the California coast produces hot SAWs. Cold SAWs result from anticyclonic Rossby wave breaking over the northwestern U.S. Hot SAWs are preceded by warming in the Great Basin and dry conditions across the Southwestern U.S. Precipitation over the Southwest, including SoCal, and snow accumulation in the Great Basin usually precede cold SAWs. Both SAW flavors, but especially the hot SAWs, yield low relative humidity at the coast. Although cold SAWs tend to be associated with the strongest winds, hot SAWs tend to last longer and preferentially favor wildfire growth. Historically, out of large (> 100 acres) SAW-spread wildfires, 90% were associated with hot SAWs, accounting for 95% of burned area. As health impacts of SAW-driven coastal fall, winter and spring heat waves and impacts of smoke from wildfires have been recently identified, our results have implications for designing early warning systems. The long-term warming trend in coastal temperatures associated with SAWs is focused on January–March, when hot and cold SAW frequency and temperature intensity have been increasing and decreasing, respectively, over our 71-year record.